The characteristics and preparation of the antibiotic lincomycin are disclosed in U.S. Pat. No. 3,086,912. Clindamycin is disclosed in U.S. Pat. No. 3,496,163. These antibiotics have been extensively used as medicines in humans and animals. A number of patents world-wide have issued concerning these antibiotics and a variety of derivatives thereof.
The structural formulas for lincomycin (1) and clindamycin (2) are shown in Chart 1.
The lincomycin- and clindamycin-type compounds which can be converted to the 3-(5'-adenylate) are shown in Chart 2. In place of the hydroxyl at the three position of the lincosaminide moiety, there is substituted the adenylate residue.
The 3-(5'-adenylate) of the subject invention can be prepared by microbiological transformation procedures. A 3-(5'-adenylate) is shown in Chart 3. This compound, designated U-63,440, is used to exemplify the other compounds which are within the scope of the subject invention, as shown in Chart 2.